Organic peroxide compositions



Patented Oct. 18, 1938 Franz Rudolf Moser, Amsterdam,

signor to Shell Development Company,

Francisco, Calif.,

No Drawing.

San

a corporation of Delaware Original application March 18,

1935, Serial No. 11,667. Divided and this application July 6, 1937, Serial No. 152,141

'7 Claims.

This invention relates to aldehyde and ketone peroxides and deals with new compositions of matter comprising these peroxides suitably wetted to reduce their explosiveness and render them capable of safe handling, transportation and storage.

This application is a division of my co-pending application, Serial Number 11,667, filed March 18, 1935, now U. S. Patent No. 2,092,322.

Aldehyde and ketone peroxides have many desirable properties and extensive potential uses, but they have been applied industrially on only a very limited scale because of their explosiveness and inflammability. The hazards involved in their use have led to the introduction of nonexplosive substitutes such as peroxy-pyrophosphate compounds of formaldehyde and the like which because of their inorganic content, are less desirable for most of the purposes for which aldehyde and ketone peroxides are particularly adapted.

I have found that the disadvantages of aldehyde and ketone peroxides may be greatly reduced and that these peroxides may be made safe for handling, provided ordinary precautions are observed, by adding thereto a suitable hydrocarbon in sufficient quantity to wet their surfaces. Aldehyde and ketone peroxides so treated may, in most cases, be applied in the same way, to the same uses, as the pure or unwetted peroxides but because of their greater safety they have a greatly enhanced usefulness and Wider applicability.

While the amount of hydrocarbon which will be required to render a particular aldehyde or ketone peroxide safe in handling will depend, among other factors, upon the state of subdivision of the peroxide, in all cases only minor amounts are necessary and, in general, only about 10% to 50% of hydrocarbon, based on the weight of the final product, need be used. A wide variety of different hydrocarbons or hydrocarbon mixtures, may be used as wetting agents in accordance with my invention. Normally liquid or relatively low melting hydrocarbons are preferred and most.

preferably hydrocarbons boiling above about 100 C. are used as their lower volatility reduces their fire hazard. However, where the contemplated use demands that very pure aldehyde and/or ketone peroxides be employed, as for example, in the bleaching of flour, and the like, more volatile hydrocarbons which may readily be removed by distillation or other means, immediately prior to application of the peroxide, may be used as wet ting agents. Typical hydrocarbons which may be used in preparing the organic peroxide compositions of my invention, include therefore gasoline and lower boiling hydrocarbon fractions, benzene, gas oil, and the like, for example.

The hydrocarbon wetting agent may be added to the peroxide at any time during or after its manufacture and most preferably is added during the manufacturing process itself, as described in my co-pending application previously referred to, as additional protection for the manufacturing plant is secured thereby. In any case a thorough, intimate dispersion of the wetting agent throughout the peroxide mass is highly desirable.

Aldehyde and ketone peroxides obtainable from the following compounds are rendered more inert and less explosive by incorporating therewith minor amounts of hydrocarbons; aliphatic ketones, including, acetone, methyl ethyl ketone, diethyl ketone, methyl isopropyl ketone, methyl tertiary butyl ketone, aromatic ketones including aceto-phenone, benzo-phenone, benzyl-ethyl ketone, benzylnaphthyl ketone; the aromatic aldehydes, benzaldehyde, toluic aldehyde, cuminol and naphthaldehyde, aliphatic aldehdyes including formaldehyde, acetaldehyde, isobutyraldehyde, methyl ethyl acetaldehyde, trimethylacetaldehyde, aldehyde-ketones including pyroracemic aldehyde, isopropyl glyoxal, formyl acetone, laevuline aldehyde, benzoyl-propia-aldehyde and polyketonic and polyaldehydic compounds, as diacetyl, acetyl propionyl, acetyl acetone, acetonyl acetyl acetone, glyoxal, succinic dialdehyde, mesoxalic dialdehyde, benzoyl-acetyl, phenyl-methyl-tri-ketone and substituted aldehydes and/or ketones including chloral, monoand polychloracetone, m-nitrobenzaldehyde, and the like. Either the pure individual aldehyde or ketone peroxides or mixtures of such pure compounds may be used in preparing the compositions of my invention, or cruder peroxides containing contaminants acquired during manufacture or use may be employed. In either case the addition of hydrocarbon wetting agents yields products which can be handled and stored with greatly reduced risk of explosion. Furthermore, other materials, such for example, as suitable stabilizing agents, may be added to my novel compositions to prevent deterioration of the peroxide content during storage, etc., without nullifying the advantages conferred thereon by the hydrocarbon wetting agent.

The products of my invention have many uses aside from those already mentioned. They may be directly added to Diesel engine fuels and gasolines as primers and ignition aids. They are useful intermediates in the preparation of pharmaceuticals and other synthetic organic products. They may be used as oxidizing agents for promoting the drying of paint and varnish films and as catalytic agents as in the control of the addition of halogen acids to unsaturated compounds, etc.

While I have in the foregoing described in some detail the preferred embodiment of my invention and some variants thereof, it will be understood that this is only for the purpose of making the invention more clear and that the invention is not to be regarded as limited to the details of opera tion described, nor is it dependent upon the soundness or accuracy of the theories which I have advanced as to the reasons for the advantageous results attained On the other hand, the invention is to be regarded as limited only by the terms of the accompanying claims, in which it is my intention to claim all novelty inherent therein as broadly as is possible in. view of the prior art.

I claim as my invention:

1. An organic peroxide composition essentially comprising a peroxide of the class consisting of aldehyde and ketone peroxides and a minor amount of a hydrocarbon in the liquid state sufficient to wet the peroxide surfaces.

2. An organic peroxide composition essentially comprising a peroxide of the class consisting of aldehyde and ketone peroxides and a minor amount of a liquid hydrocarbon boiling above 100 C. at least suflicient to wet the peroxide surfaces.

3. An organic peroxide composition essentially comprising a peroxide of the class consisting of aldehyde and ketone peroxides wet with 10 to by weight of a normally liquid hydrocarbon.

4. An organic peroxide composition essentially comprising a peroxide of the class consisting of aldehyde and ketone peroxides wet with a minor amount of gas oil at least suflicient to wet the peroxide surfaces.

5. An organic peroxide composition essentially comprising an aldehyde peroxide and a minor amount of a liquid hydrocarbon at least sufficient to Wet the peroxide surfaces.

6. An organic peroxide composition essentially comprising a ketone peroxide and a minor amount of a liquid hydrocarbon at least sufficient to wet the peroxide surfaces.

'7. An organic peroxide composition essentially comprising acetone peroxide wet with 10 to 50% by weight of a liquid hydrocarbon.

FRANZ RUDOLF MOSER. 

